Production of alpha-amino anthraquinones



Patented Jan. 24, 1928.

UNITED STATES PATENT "OFFICE.-

.JOHN THOMAS AND ARTHUR HUGH DAVIES, CARLISLE, ENGLAND, ASSIGNORS To SCOTTISH DYES, LIMITED, 01: CARLISLE, CUMBERLAND, ENGLAND.

rnonuc'rro'n or ALPHA-Ammo Anrnnseumonn'sfl No Drawing. Application fi1ed-Ju1y 20, 1921, Serial No. 486,249, andin Great Britain. July 23, 1920.

This invention relates to theproduction of dyestufi intermediates and particularly of amino-anthraquinones.

The'us'ual method for the production of 2-amino-anthraquinone is by autoclaving the sodium salt of anthraquinone-Q-sulphonic acid, commonly known "as silver salt with aqueous ammonia, method is used for the preparation of 1-' amino-anthraquinone the yields are cons1dcrably lower'and the product is of an inierior' quality. 3 i 1' V The present invention, is based upon the observation that 'l-amino-anthraquinone. (on. amino-anthraquinone) of good quality can be obtained by autoclaving lfchlorzuithraquinone (1x chlor-anthraquinone) with aqueous ammonia'and upon the fur-z ther observation that while if anthraqum- I one-disulphonates'are autoclaved with am-' monia the'yields generally tend to be unsatisfactory, by autoclaving the dichloranthraquinones with, ammonia the, corresponding diamino-coinpound can be obtained with perfectly satisfactory results.

The invention consists broadly in producing amino-anthraquinone by autoclaving with'ammonia halogen derivatives of anthra-quinone in which onlyhydrogens in the a position in the aromatic nucleus are sub:

stituted and such hydrogens are substituted by halogen atoms.

The invention also comprises the employ .ment of copper in the form, for instance, of a salt of copper for. promoting the desired reaction. i

The following particulars are given by way of example inorder to illustrate a. suit able manner of carrying thednvention. into effect. r

' 100 parts of vl-chloran|.-hraq1 iinone (occhlof-anthraquirione) are heated with 700 parts of 26% ammonia to 17 0 C- for twelve hours. The vessel is'then allowed to .cool

and the product worked up in the usual way. The yield-'of -amino-anthraquinone If the same approaches the theoretical, and the qualityis excellent. The presence of small amounts anthraquinones which comprises autoclav ing with ammoniahalogen derivatives of anthraquinone in which only hydrogens in the on position in the aromatic nucleus are substituted and such hydrogens are substituted by halogen atoms.

2. The process of producing amino-anthraquinones which comprises autoclaving with ammonia and copper compounds halogen derivatives of anthraquinone'in which only hy'drogens in the a position in the aromatic nucleus are substituted and such hydrogens are substituted by halogen atoms.

3. The process of"producing amino-anthraquinones' which comprises- 'autoclaving" with ammonia chlorinederivativesof an-.

thraquinone in. which only hydrogens in the a position in the aromaticnucleus are'substituted and such hydrogens are substituted by chlorine atoms.

4. The process of producing amino'-anthraquinones which" comprises autoclaving with ammonia and copper eompoundschlm rine derivatives of anthraquinone in which;

only hydrogens inthe' on position in the aro-- matic nucleus. are substituted and such hydrogens are substituted by chlorine atoms.

5. The process of producing a-amino- .anthraquinone which comprisesautoclaving with ammonia wchlor-anthraquinone.

6. The process of producing a-amlnoanthraquinone which comprises antoclaving with ammonia and. a copper compound a-' chlor-anthraquinone.

In testimony whereof we havexsigned our names tothis specification. y

JOHN THOMAS. v ARTHUR'HUGH DAVIES. 

